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Find luxury hotels in Chesterton, IN

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Top Chesterton Luxury Hotels

Waterbird Lakeside Inn

2.0 star property
Chesterton
8.2 out of 10, Very Good, (984)
"Balcony was a nice extra. Room was clean and bed was comfortable. I’d stay here again if in the area"
United States
Jorge
$90 nightly
The price is $101
Dec 1 - Dec 2
Total with taxes and fees
Waterbird Lakeside Inn

Quality Inn Chesterton near Indiana Dunes National Park I-94

2.5 star property
Chesterton
8.0 out of 10, Very Good, (715)
"Clean room, easy check in"
United States
Billy
$77 nightly
The price is $86
Dec 31 - Jan 1, 2026
Total with taxes and fees
Quality Inn Chesterton near Indiana Dunes National Park I-94

Best Western Indian Oak

2.5 star property
Chesterton
8.6 out of 10, Excellent, (1015)
"It was very nice, with great access to the national park."
United States
leona ann
$93 nightly
The price is $105
Dec 7 - Dec 8
Total with taxes and fees
Best Western Indian Oak
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Find out more about Chesterton

Chestertonand its attractions for luxury travelers

Nestled near the scenic shores of Lake Michigan, Chesterton, Indiana, offers a blend of outdoor beauty and cultural experiences that luxury travelers will appreciate. Start your journey at the Indiana Dunes National Park, where you can explore the stunning sandy beaches and towering dunes, perfect for a relaxing day of sunbathing or a hike with breathtaking lake views. Art enthusiasts will find inspiration at the nearby Chesterton Art Center, which showcases local talent and hosts workshops for those interested in honing their creative skills. For a unique shopping experience, visit the Chesterton European Market, held seasonally, where you can browse artisanal goods and gourmet food while enjoying a vibrant community atmosphere. After a day of exploration, unwind at the local wineries, such as the nearby Sand Creek Winery, which offers tastings and stunning views of the vineyards. When it comes to accommodation, consider staying in the charming downtown area where boutique hotels provide a cozy yet upscale experience, complete with personalized service and easy access to the town's highlights. Enjoy your stay as you indulge in the local cuisine at fine dining restaurants, making your trip both luxurious and memorable.

Top Chesterton Hotel Reviews

Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway to Chesterton?
Let Expedia help you arrange your flight to Chicago Midway Airport (MDW) airport or Chicago O'Hare Intl. Airport (ORD) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Chesterton offers. Known for its restaurants, Chesterton also has some interesting things to see and do including Lake Michigan, so you may want to take in the local sights during your visit.
When can I expect good weather in Chesterton?
Planning for the weather is an important factor for making your trip to Chesterton a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.
What's there to see and do in Chesterton?
Enjoy Chesterton and visit Lake Michigan, Lustron House, and Chellberg Farm. If you have extra time while you're in the area, you might want to see Indiana Dunes Visitor Center and Bailly Homestead - American Indians and Fur Traders.

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